Rob and Jenny's Second Date - No. 2

Rob:  See you there then. Don’t forget to wear the dress I asked for.

Jenny: Of course :-) See you tomorrow! Can’t wait!

Nearly six weeks after our first date I was back in New York. It was late spring and the weather was perfect - sunny, warm but not too hot.  Since last time, Jenny and I had exchanged regular text messages, nothing about sex but rather generalities like how we had had fun last time, how her work or my work was going, and such like. We had also firmed up on a date to meet up again - and the practicalities: how much I would give her as a present. A bit more than last time, but not much.

This time I had organised my schedule to finish my meetings in Midtown early on a Friday and fly back on the Saturday evening flight, so that we could meet up for lunch and take it from there.  I’d picked a nice seafood restaurant in Midtown and planned a little shopping trip after.

I arrived early at the restaurant and got myself comfortable with a good view of the street and pavement outside, and a line of sight to the entrance, looking forward to the view as she arrived. She was to wear a nice cotton summer dress - “showing enough, but not too much” as I had put it.
  

As it happened, I got a great view of her walking down the street towards the entrance. The dress was lovely: simple straps, v-neck cleavage, cinched at the waist and flaring out gently to where it ended just over half way down her thighs.  It looked perfect on her, with her blonde hair flowing down to her shoulders.   As I would have expected from her, it was just perfect.  And it fit my plans perfectly as well.

We caught up on banalities and work over ceviche starters, with a pricey but good bottle of dry white wine (I took the waitress's recommendation for once).  She seemed to be enjoying her job at the travel agency, but having some office office politics issues with her supervisor.  I sagely gave her some advice on how to manage the situation.

Once the waitress had cleared away our starters I pulled a small case from my jacket pocket. “A small present for you Jenny. You should put it on”.  I slid the case across the table to her and she picked it up and opened it.  The look on her face was one of mild shock as she took it in.
 

It was a black choker, made of soft, shiny leather and about half an inch wide. Around it were rounded gold studs and on the front hung a gold ring from a central hinge. The ring was about an inch or so in diameter, so that the bottom rim of the choker made a line through its centre. From the ring hung a small naked female figurine, hands holding on to the ring, wrists tied together and legs hanging with toes down.
  

She stared at it for a while, then looked at the locking mechanism at the back. Then asked “can you help me put it on? I’m not sure how….”  I stood up and went behind her. She gathered her hair to one side and held it away from her neck. From my vantage point I could not but admire the plunging cleavage as I fastened the choker. I made sure the fit was good, but not tight, and went back to my seat, leaving Jenny to fix her hair, as it had been before with some flowing down the front of her shoulders.
 

“Make sure it’s nicely visible, no hiding it behind your hair now Jenny.” She adjusted her hair to flow down her back only.  Just then, with perfect timing, our waitress came back with our mains.  I watched her face as she took in the choker, blushing and looking away quickly.  I smiled at Jenny, who had also developed some new pink shading on her cheeks.

“Do you have some scrunchies so you can make sure the hair stays back?” I asked.  “It would be a shame if people didn’t get to admire it.”  She did, and after a moment rummaging through the handbag, her hair was soon neatly secured behind her back.

I moved the subject back to life and work as we enjoyed our mains. Just after asking for the bill I told what I had planned next. “I promised a shopping trip and I had a pretty special place in mind. But before we can go there, we need to get you a more appropriate dress than this”.  She looked shocked. After all, I had made a point of complimenting her profusely when she arrived.  “Is there a department store near here?” I asked, knowing the answer full well.  Jenny answered correctly and we headed to the store.

I didn’t have any major preference or plan for what to buy. I wanted to see her change into different things and decide what to get from that.  We roamed the relevant sections of the store and I picked dresses I liked the look of, or not, as we went. Some nice, some a bit on the slutty side. I didn’t fancy wasting time on anything prudish though.

She tried it all on. Short and skimpy to show off those long legs. A couple of figure hugging short cocktail dresses and some with more cleavage than coverage.

After a good dozen or so dresses I made up my mind and chose another summer dress for her. It was a couple of inches shorter than her own dress but crucially was also very low cut and open at the back. I paid and sent her back to the changing room with instructions - “you probably shouldn't wear your bra with that”.

She didn't disappoint.  The dress was stunning, and her breasts were more than capable of coping with the lack of support. I complimented her looks, gave her a peck on the cheek and guided her back out of the store.

* * * * * *

By design, our next stop was not too far away. So we walked and enjoyed the New York spring weather.  I didn’t tell her where we were going, but I can’t say she looked too surprised when we stopped outside of Agent Provocateur. I admired the window display for a few seconds, then said “let’s get some more exciting things for you to wear”.

At first we browsed like any couple. Looking at bras and panties, discussing which looked nice and which ones she didn’t like.  I picked a couple of sets that she liked, a matching blue bra and knickers and a red set in the same style. 

I then spotted a  “Rubi Playsuit” and made a little show of looking it over, before adding to our shopping. It wasn’t cheap, but I was happy spending.  I then added a metallic choker, rose gold colour, with a leash and a set of double hand-cuffs with a long chain.
  

Jenny didn’t flinch at my choices as far as I could tell, but she did have a permanent blush in her cheeks, as her choker and cleavage had received some not so subtle looks, from both sexes. Her hard nipples strained against the soft cotton dress, very noticeably.  I asked her to hold the choker and cuffs as we went to the till to pay.  The bill was quite something, and I’m sure she noticed it was quite a bit more than our agreed “gift” to her.

As my hotel was several blocks away, I hailed a yellow cab.  The drive was uneventful and we arrived soon enough. The hotel was more upscale than last time, reflecting my intention of having even more fun, and frankly my appreciation of Jenny. I can’t say whether she appreciated the gesture or not.
 

We shared the elevator rid up with a teenage girl, who had clearly noticed the middle aged man with the well proportioned younger lady and the unmissable choker.  For fun, I put my hand on Jenny’s back, then slid it down her dress and under, allowing the hem to lift noticeably as I cupped her cheek and enjoyed an unsubtle fondle.  The girl turned bright red, trying her best to look elsewhere - not easy in an elevator with mirrors on three sides. As we got to our floor, I removed my hand but I couldn't resist a knowing smile at the girl as we exited and headed to my room.

* * * * * *

The room was on the 42nd floor, with floor to ceiling windows providing a stunning view, in places all the way to Downtown.  It was large, with a large bathroom on the left as you entered, a king sized bed as well as a sofa and two comfy chairs and a good sized desk.

Jenny walked to the window to take in the view and I soon joined her, standing behind her with a hand on either shoulder.  I turned her around and put a hand behind her head and kissed her.  It was gratifying to finally have some intimate contact (not counting the elevator ass grope) and I could have lifted her onto the desk and fucked her there and then. But age brings patience, and I wanted to enjoy this. It was only early in the afternoon after all, and we had all night.

“Why don’t you give me a little fashion show. You can start with the blue ones. Get changed in the bathroom.” She grabbed the Agent Provocateur bag and went to the bathroom, and I sat down in one of the comfy chairs.  The blue set looked great on her as she came out. A pretty bra and panty set, elegant and well designed.  “That looks great on you” I said, before adding “let’s see if the red ones are as nice.”  Again she went to change in the bathroom.

The red set was the same design, and I must say I preferred the blue set, to match her eyes and complement the blonde hair. But we had business to attend to; I had a set-up from earlier to complete. “This is also nice, but you need something red to go with it” I said.  “Come here”, I patted the arm of the chair and she walked over. “On my lap!”, I guided her to lie down, with her ass facing up on my lap.  “Your dress didn’t please me. A fitting punishment would be to match your ass to the panties, don’t you think?”.  “Yes Master” she replied, before adding “I’ve been bad.”

I stroked and squeezed her buttocks casually, enjoying the firm, but soft and smooth feel.  For now I left the panties on and gave her right cheek a light smack with my right hand. Then her left cheek, again not too hard.  I played around a bit more, sitting comfortably with her draped over my lap. Then a harder smack, right, then left, then repeated again three times on each side. A light redness came up, and I found myself comparing the colour of her butt to the red panties.  I had not intention of going quite that far, but found the comparison amusing.
  

I massaged a bit more, then added three more hard slaps on either side.  Jenny let out a little whimper, which I took as a cue to ask “do you feel sufficiently punished now?”. I was curious to find her limits, and frankly enjoying the groping more than the spanking.  “No Master,” she replied, “I disappointed you too much with my ugly dress”.  So there it was.  I simply replied: “well, we can’t have you living with that guilt unpunished.”

The spanks themselves were hard enough, I thought, so I went with more rather than harder. Five times each side, then five more each after a little bit more groping.  She was turning a brighter red now, and over a larger area, as I had spread my spanks out.  I decided it was time to slide her panties down her legs, to rest on her ankles. There I twisted them around and tied firmly enough to stay put, and added five more spanks on either side.

Her pussy was visibly moist, and I slid my hand over it back and forth, eventually adding my middle finger between her lips to tease her clitoris.  “Does that teach you to dress appropriately in the future, Jenny?” I asked.  “Yes Master.  I will not let you down again. Please give me a chance to please you.”  I grabbed her butt cheek in my left hand, fondling as I continued the pussy play with my right hand.  It was a feast for my hands and as she shuddered into an orgasm, clearly it had worked for her too.

My intention had been to get her into the Ruby Playsuit at this point. Instead I reached down to undo her bra and told her to stand up. She positioned herself to face me, arms by her side.  I stood up to face her.  “Undo my shirt” I commanded, and she stepped forward immediately and started unfastening buttons. Once the shirt was open I told her to kneel and undo my belt, then trouser buttons and fly.  She looked up at me expectantly, kneeling naked, bar the choker, hands by her side.  “I want the best blowjob you have ever delivered”, I said firmly. She didn’t need to be told twice and tugged my trousers and boxers down, opened her mouth and teased my cock in.

I can’t say if it was her best blow job ever, or frankly if it was the best I had enjoyed.  But it was good.  Keeping my hands to myself, I left her to work while I stood looking down at her head moving back and forth, and mouth sucking on my dick.  She kept her hands down, presumably remembering how I like it.  Eventually I moved back a step, my dick pulling out of her mouth as she tried to follow, and sat down on the chair again.  “Take my socks off” I ordered, and when she had finished, continued with “and the trousers.”  Once the trousers were off, she made to continue the blow job. I put my hand up to stop her: “There’s a bottle of scotch on the desk and glasses. Pour me some with ice. Crawl there, but you can walk back”.
  

She crawled on all fours to the desk, her ass swaying and her pussy glistening.  At the desk she stood up and poured the whisky and asked “how much ice Master?”  Such a thoughtful girl I thought, before replying “normally not a lot, but put in a handful this time.” She returned to my chair with the glass flat on her palm, supported by her other hand, and handed it to me demurely.  I took a sip, then rested the glass on the arm of the chair.  “You can continue now”, then, “make sure you swallow it all, you shouldn’t waste your master’s cum.”

On her knees in front me, she continued.  I relaxed and sipped my scotch, content to let her service me.  She kept a good and steady pace, not trying to rush things but also not lazy.  My cock mostly stayed in her mouth, very occasionally coming out to be licked and guided back in with her head and tongue.  It was only when I put the empty glass down on the chair arm with an audible sigh, and leaned back with my arms behind my head, that she increased the pace and intensity.  It wasn’t long before I came, and came big - both the intensity of my orgasm and the size of the load.  She kept her mouth around the head and continued softly, trying to make sure to get it all. But I started to stand up, and as she moved back I ejeculated a small blob onto her face. “Tsk…. sloppy work, Jenny.  We’ll put this one in the bank for some punishment later. Go clean up now and put on that playsuit”.

While she was in the bathroom, I put my boxers back on and buttoned a couple of buttons back up on my shirt.  When she came out I almost laughed at the futility of that suit. She was gorgeous and had the most perfect figure I had ever seen, an outfit that covers nothing frankly did nothing for her.  But she had left her choker on, good girl that she was, but it sat uncomfortably with the neck piece on the suit. It had a vertical chain from the neck strap down to a couple of springs that highlighted her slim waist, all ending in a few strings making the shape of panties, without any of the covering bits..

I told her to spin around for me, and stood up to have a good feel of the suit and her body - cupping and groping her breasts and buttocks at my leisure.  I took a step back and said “shouldn’t you be thanking me for buying you such pretty things?”. She looked uncertain, presumably given that she had just finished giving me a blow job.  But then she knelt down on the floor, resting her buttocks on her heels and said “Thank you Master. You have been so generous to me.  I will do anything for you, to thank you.”  I smiled at her quick thinking.

“Very well,” I continued, “you can stand up and take that thing of”, as I gestured up and down at the play suit. She undid it, and soon stood naked again.  “You can start by giving me a little show.” I said, and turned to open the bedside table drawer, where I had put a handful of toys brought from the UK.  I handed her a large rubbery dildo and a tube of KY gel.  I pointed to the bed and said “kneel in the middle of the bed”, and while she did I moved one of the chairs to a comfortable position facing the bed.

“Lube it up!” - a command she quickly obeyed, squirting some gel over the dildo and rubbing it on.  She’d clearly heard the word ‘show’ clearly and made a nice sexy performance of stroking the cock-like dildo.  “Why don’t you taste it?” I said, and watched as she stuck her tongue out just a little bit and flicked it over the head of the dildo.  “I think he’s ready to go in now.”

She inserted the dildo into her pussy, still kneeling on the bed, and soon it was moving in and out in decent strokes.  “You can play with your breast”, so her left hand moved to cup her breast and pull on her nipple, then the same with the other breast.  I watched her fuck herself like this for a couple of minutes, then “you can lie down now, feet to me”. She lay down, dildo in her hand but did nothing. “You can continue now and use your left hand on your clit”.  She wasted no time in complying and thrust the dildo in and out quite vigorously, whilst her clit got no less attention.  “Slow down” and “you should pull on your nipples again”, she shuddered at that, but slowed down and moved her left hand up to her chest.

We played this game for a little while.  I let her go faster, slower, at her own pace, suck on the dildo while masturbating or playing with her tits.  Eventually I let her go at her own pace and gave her permission to cum.  She did, albeit not as quickly as I had expected.  She also remembered her lesson from the previous time, and continued her masturbation, ever so slowly, even after she had come.

“You did well Jenny.  You can stop now.”  She did, letting out a loud sigh, and lay where she was clearly catching her breath.  I went to the Agent Provocateur bag and took out the choker and cuffs and put them in the bathroom.

When I came back into the room I looked at her and said “go and clean up. Put your hair in a high ponytail like last time, and put on the other choker and handcuffs”.  She got up and went to the bathroom.  I sat back down in the chair and waited the couple of minutes she spent getting ready.
  

And ready she got. The rose gold, metal choker looked great.  The leash fell down between her breasts. She held her arms straight down, so that the chain between the cuffs curved down and jingled a little as she walked towards me.  She was the perfect vision of a sexy slave.  “Get me another drink” I ordered, and, no questions needed, she complied quickly and brought it over as before.  I took a sip, then pointed to the floor behind her and told her to kneel there.
 

“Open your mouth”, and then immediately I stood up and took the step towards her, taking my dick out of my boxers and directly into her mouth. She then set to work as I stood there.  Before long I reached down to hold onto the leash, looping it around my thigh, so that she was limited in how far back she could go.  I gradually pulled the leash in, so that she was stuck with my cock deep in her mouth and only a little room to move back and forth.
 

Letting out the leash a bit again, to give her a breath, I put my other hand on her ponytail and held her head still as I started thrusting.  I then let go of the ponytail and looped the leash back around so that I could hold on to it as I reached for my drink. I took a sip, then removed an ice cube from my mouth.  With my other hand, still holding the leash, I lifted her chin up and caressed the icecube over her lips, then down her chin and neck towards her chest. I traced a line, first to the right nipple and around it, then through the cleavage to the left nipple where I repeated the move. Finally I painted her lips again with the cube and pushed it into her mouth.

“You can get on the bed now” I said as I let go of the leash, “on all fours”.  She positioned herself perfectly in the middle of the bed, so that I had enough space to climb up behind her. I reached round to grab hold of the leash again, then guided my cock into her pussy.  Still holding the leash, I grabbed hold of her hips with both hands and started thrusting, alternating hard, deep thrusts, with shorter and gentler ones.

I then moved her to lie on her back, and lay down on my side next to her and entered her pussy again, using the leash to pull her head towards me for a kiss and the other down to play with her clit.  She came eventually, or pretended to, and I followed swiftly.  We then lay there, spooning for some time.

I was starting to fall asleep, when I roused myself and got out of the bed and to the bathroom.  A splash of cold water on the face woke me up well enough, and I returned to the bed.  “Time to get up Jenny”, clearly younger and fitter than me, she seemed to either not have been as tired or have shaken it off quicker, as she quickly got up and stood in front of me. “Kneel again”, which she did.

“You wasted some of my cum earlier.” I continued “which still needs to be punished. But I’m tired now, so have decided that you should administer your own punishment.” She looked up at me blankly. I circled around her, then bent over to casually cup and squeeze her tits, then rolled and pulled on her nipples.  “Pull on your nipples, as hard and as long as you think you need, to make up for insulting your Master.”  She did as she was told, put each nipple between a thumb and index finger and, clearly pulled slowly, until she reached a point. “A bit harder I think”, I said, and saw her pull  further.

I left her to it and went to the bedside table and opened the drawer, removing some objects, which she couldn’t see, and placed them on the bed. 

When I got back to her, I could see tears rolling down her face. Still she kept up the pull on her nipples. I waited a moment, then told her to “let go now; we wouldn’t want this turning into pleasure, now would we?” She let go, but not with the relief I had expected. I reached down two cup her breasts again, squeezed and said “and I certainly don’t want these damaged.” With that I stood and walked to the bed. “You can come over here now”.  She stood and turned, the metal choker and cuffs still on.

On the bed I had placed a plastic dildo, smaller and harder than the one she had used before, and a butt plug.  I watched her face to see if she recognised it, but didn’t sense any reaction.  “Get on all four on the bed” I told her. She knew what to do, and was soon on all fours.  I turned the vibrator on and started stroking it against her pussy. Then had an idea, and traced it up, past her anus, and along her spine. When I reached her upper back, I circled back around and let the vibrator buzz against her nipple. First one, then the other.  That caused a clear reaction as she moaned and tried to move, before stopping herself.
 

At that I gave her a playful but hard slap against her ass, and then continued playing the vibrator against her pussy.  Around the clitoris, and into the vagina. I pushed it in, most of the way, until it stayed and said “keep it there”, while I picked up the butt plug. I squirted some KY gel against her anus, and gently pushed the plug in.  She made a brief move down, but ultimately stayed in position.
 

I moved back to the dildo and continued fucking her with it, slowly but in long, deep moves. I moved my other hand to the butt plug and teased it gently at the same time.  She started moaning and I increased the pace.  “You can play withourself now” I said, and she wasted no time to start masturbating her clit.  We kept going for close to five minutes, while I alternated the thrusts of the dildo and increased or decreased the intensity on the butt plug.  Finally she came with a loud moan and a shudder, and, to my surprise, a pleading “please, stop, please stop….” and then a belated and quiet “....please stop Master.”  She kept up some pretense at masturbating, while I kept her waiting, then pulled the vibrator out and told her “you can stop now.”

She collapsed on the bed, breathing deeply. Perhaps oblivious to the butt plug still in position. I let her rest for a minute or so, before removing my shirt and boxers and climbing onto the bed.  She was familiar with my move, and moved round to take my cock in her mouth.  I took hold of her ponytail and leash again to take control of the blow job, and used my position to fuck her mouth, albeit relatively gently.  I let go of her and pulled out, and gave her butt a sharp spank.  She understood the wordless command and got back on all four.

I positioned myself behind her and entered her pussy.  She was still wet and I wasted no time to move up the tempo and hardness, with no concern for running out of steam, hands on her hips, grabbing flesh and one thumb on the butt plug. I had every intention of fucking her as hard as I could for as long as I could.

Finally as I started tiring, but before I had to slow down, I slowed down in a casual , controlled way and started rubbing the butt plug more intensely.  I then pulled it out carefully, and squeezed some more KY on her ass hole before pulling out of her pussy, and putting my cock into position.

I reached around to grab the leash, then slowly pushed my cock into her ass.  She was remarkably quiet and kept her position without me having to hold her back, although I did have a good grip on her hips.

As expected she was incredibly tight, and I slowly increased the pace of gentle, short thrusts, while grabbing the leash tightly and pulling.  Then deeper and harder, until I felt her tense up. We went round a few circles like that, until I came for the last time that evening.

After I pulled out, we spooned again for a few moments, before heading for the shower, together.  By now it was late evening and hunger made itself known. We ordered room service and ate together, naked on the bed.

* * * * * *

She stayed the night and I woke up to the glorious sight of her drying herself with a towel, standing at the foot of the bed.  I adjusted myself to lie flat, legs apart, and pulled the cover off.  She took the hint without hesitation, and climbed up along my legs and took my soft cock in her mouth.  It was a delightful morning blow-job, after which we got dressed and headed out for breakfast. To my satisfaction, she had put on leather and gold choker again, and kept her hair back.

I expected that to be it for this trip, but my flight wasn’t until late in the evening and it was only 9am.  Over breakfast in the hotel restaurant, she dropped the bombshell:  “Rob, do you remember my friend Lexi? You asked me about her - she was in one of my pictures.”  I nodded, not sure where this was going. Jenny continued, “I tell her everything, she knows most of what we did last time.  She’s curious to meet you.”

TO BE CONTINUED...